Potassium Carbonate → 6-Chloro-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine

HRID 2401232Notes

Reaction equation

HRID 2401232 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:21])([F:20])[C:9]1[NH:19][C:12]2=[N:13][CH:14]=[C:15]([CH2:17][NH2:18])[CH:16]=[C:11]2[CH:10]=1.[Cl:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[CH:25][N:24]=1>CS(C)=O>[Cl:22][C:23]1[N:24]=[CH:25][N:26]=[C:27]([NH:18][CH2:17][C:15]2[CH:16]=[C:11]3[CH:10]=[C:9]([C:8]([F:7])([F:20])[F:21])[NH:19][C:12]3=[N:13][CH:14]=2)[CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 513561316-Chloro-N-{[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (106 mg, 0.767 mmol) was added to 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 75 mg, 0.349 mmol) and 4,6-dichloropyrimidine (104 mg, 0.697 mmol) in DMSO (2 mL). The mixture was heated at 120° C. for 1 hour in the microwave. Crude LCMS showed desired product and no starting material left so the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. This solid was dissolved in a mixture of acetonitrile and DMSO (1:1, 1.8 mL) and purified by MDAP. Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound as a brown solid (24 mg);

Sources & evidence

ORD record
ord-dcd53762457c485089b0014159169f10
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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